3-(1,3-苯并噻唑-2-基)苯酚 | 25389-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 3-(1,3-苯并噻唑-2-基)苯酚
• 英文名称: 3-benzothiazol-2-yl-phenol
• 英文别名: 3-(benzo[d]thiazol-2-yl)phenol；2-(3-hydroxyphenyl)benzothiazole；3-(1,3-Benzothiazol-2-yl)phenol
• CAS: 25389-28-0
• 化学式: C₁₃H₉NOS
• mdl: MFCD03680993
• 分子量: 227.287
• InChiKey: JIWVTDBBMGSTFI-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  431.2±47.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(1,3-苯并噻唑-2-基)苯酚 在 potassium phosphate 、 copper(l) iodide 、 N¹-benzyl-N²-(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide 、 四丁基溴化铵 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 108.0h， 生成 Pt(pbthz)
  参考文献：
  名称：

  通过苯并氮杂环和中心金属调节四齿 Pd(II) 和 Pt(II) 配合物的激发态

  摘要：

  一系列四齿Pd(II)和Pt(II)配合物，含有5/6/6金属环与苯基N-杂芳基苯并[ d ]咪唑( pbiz )、苯并[ d ]恶唑( pboz )或苯并[ d ]噻唑( pbthz ) 含配体被开发出来。通过实验和理论计算的系统研究表明，中心金属和苯并环化的N-杂芳环对 Pd(II) 和 Pt(II) 配合物的电化学、光物理和激发态性质有显着影响。在相同条件下，与pbiz相比基于 Pd(II) 和 Pt(II) 的配合物，相应的金属配合物与含pboz和pbthz的配体显示出显着的红移发射光谱。与相应的 Pt(II) 配合物相比，Pd(II) 配合物表现出蓝移发射光谱。Pt(II) 配合物在其 T 1状态下具有更多的金属到配体电荷转移 ( 3 MLCT ) 特性，这使得 Pt(II) 配合物具有更高的量子效率 ( Φ PL ) 和更短的激发态寿命( τ )，导致大的辐射衰减率 ( k r

  DOI：

  10.1002/cjoc.202100641
• 作为产物：
  描述：

  间溴苯甲醚 在 magnesium 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 生成 3-(1,3-苯并噻唑-2-基)苯酚
  参考文献：
  名称：

  Thiophosphoryl-, Thiophosphoryloxy-, and Thiophosphorylamino-Benzene Derivatives as Novel Classes of Hybrid Pincer Ligands

  摘要：

  The synthetic approaches to novel families of SCE (E = S',N,O) hybrid pincer-type ligands bearing thophosphoryl, thiophosphoryloxy, and thiophosphorylamino groups in various combinations with thiophosphoryl-, thiocarbamoyl-, and imine- (including that of benzothiazole ring) donating functions have been developed. All of the ligands readily undergo direct cyclometallation (metal = Pd(II), Pt(II)) to afford 5,5- or 5,6-membered pincer complexes. Palladium complexes displayed from high to excellent catalytic performance in the Suzuki cross-coupling reaction of aryl bromides and phenylboronic acid and the higher asymmetry for a complex served as a factor of its higher catalytic activity.

  DOI：

  10.1080/10426507.2010.507726

文献信息

• [EN] NOVEL USE OF BENZOTHIAZOLE DERIVATIVES<br/>[FR] NOUVELLE UTILISATION DE DERIVES DE BENZOTHIAZOLE
  申请人：ASTRAZENECA AB

  公开号：WO2004016600A1

  公开（公告）日：2004-02-26

  The use of compounds of formula (I) wherein X, A, B, D, R1 and R2 are as defined in the Specification and pharmaceutically acceptable salts thereof in the manufacture of a medicament for the treatment or prophylaxis of diseases or conditions in which inhibition of kinase Itk activity is beneficial is disclosed. Certain novel compounds of formula (I), together with processes for their preparation, compositions containing them and their use in therapy are also disclosed.

  公开了在制造用于治疗或预防抑制激酶Itk活性有益的药物时，使用式(I)中X、A、B、D、R1和R2如规范中定义的化合物及其药学上可接受的盐。还公开了式(I)的某些新化合物，以及它们的制备方法、含有它们的组合物和它们在治疗中的用途。
• Water-promoted Dowex 50W catalyzed highly efficient green protocol for 2-arylbenzothiazole formation
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1002/jhet.9

  日期：2009.1

  aldehydes were allowed to react in one-pot operation to give 2-aryl-benzothiazoles in excellent yields in the presence of Dowex 50W in water. Very high yields coupled with the ease of work-up procedure, formation of no side products, employment of “reusable” catalyst, and “green” synthesis in aqueous medium without maintaining anhydrous reaction conditions are the most important aspects of this methodology

  在Dowex 50W的水中，以一锅操作方式使2-氨基硫酚和各种芳基醛反应，以极好的收率得到2-芳基-苯并噻唑。这种方法最重要的方面是非常高的收率，加上易于处理的过程，无副产物的形成，使用“可重复使用的”催化剂以及在水性介质中进行“绿色”合成而不保持无水反应条件，这是该方法学的最重要方面。J.杂环化​​学，（2009）。
• Compounds enhancing antitumor activity of other cytotoxic agents
  申请人：Pfizer Inc

  公开号：US06130217A1

  公开（公告）日：2000-10-10

  This invention relates to certain heterocyclic compounds and their pharmaceutically acceptable salts, which are useful for sensitizing multidrug-resistant tumor cells to anticancer agents and multidrug resistant forms of malaria, tuberculosis, leishmania and amoebic dysentery to chemotherapeutants. The compounds and their pharmaceutically acceptable salts are also inhibitors of the active drug transport capability of P-glycoprotein which is encoded by the human MDR1 gene, as well as of certain other related ATP-binding-cassette transporters from eukaryotic and prokaryotic organisms (e.g., pfmdr from Plasmodium falciprum, and murine mdr1 and mdr3 gene products).

  这项发明涉及某些杂环化合物及其药用可接受的盐，这些化合物对于使多药耐药肿瘤细胞对抗癌药物和多药耐药形式的疟疾、结核病、利什曼病和阿米巴痢疾对化疗药物具有敏感性是有用的。这些化合物及其药用可接受的盐还是人类MDR1基因编码的P-糖蛋白的活性药物转运能力的抑制剂，以及来自真核和原核生物（例如，来自疟原虫的pfmdr，以及小鼠mdr1和mdr3基因产物）的某些其他相关的ATP结合盒转运蛋白的抑制剂。
• Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents
  作者：Ernestine Nicaise Djuidje、Sabrina Sciabica、Raissa Buzzi、Valeria Dissette、Jan Balzarini、Sandra Liekens、Elena Serra、Elisa Andreotti、Stefano Manfredini、Silvia Vertuani、Anna Baldisserotto

  DOI：10.1016/j.bioorg.2020.103960

  日期：2020.8

  aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized

  氧化应激是多种多因素疾病的产物或病因。另一方面，开发多功能化合物是控制复杂疾病的公认策略。为此，合成了一系列苯并噻唑衍生物并评估了其作为抗氧化剂，防晒霜（过滤剂），抗真菌剂和抗增殖剂的多功能功效。通过2-氨基硫酚与不同的苯甲醛之间的缩合反应可轻松合成化合物。SAR研究，特别是在苯并噻唑的2位和6位上，对4g和4k的鉴定为多功能药物设计中非常有趣的潜在化合物。特别是化合物4g是在HEK 293细胞中表达的hERG钾通道的最佳阻滞剂，具有60.32％的抑制作用，IC 50  = 4.79μM。
• Pentafluorophenylammonium triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
  作者：Arup Datta

  DOI：10.13005/ojc/370112

  日期：2021.2.28

  simple and environmentally benign effective synthesis of 2-substituted benzothiazole and benzothiazoline derivatives are described in presence of PFPAT (pentafluorophenylammonium triflate) catalyst in water successfully. A series of benzothiazole derivative were synthesized by the reaction between 2-aminothiophenol and various aldehydes in good yields. Recyclability of the catalyst is observed for four

  在这项工作中，在 PFPAT（五氟苯基三氟甲磺酸铵）催化剂存在下，在水中成功地一锅、简单且环境友好地有效合成 2-取代苯并噻唑和苯并噻唑啉衍生物。通过2-氨基苯硫酚与多种醛的反应合成了一系列苯并噻唑衍生物，收率良好。观察到催化剂的可回收性四次，在水介质中其活性没有损失。